Jennifer Blackburn has held roles at Unilever, Nando's, Canadian Tire, Skip, and is now CMO of Clearly Canadian — and not one of those moves was a straight line. The pivot that surprised her most wasn't a bold leap toward opportunity; it was a quiet moment doing virtual homework with her three-year-old daughter at 3am from a different time zone, realizing the right role at the wrong time in your life is still the wrong role.

This episode is for anyone who's ever wondered whether ambition and a good life can actually coexist.

In This Episode

• Why Jennifer left a successful six-year run at Canadian Tire to join a hyper-competitive tech company — and how walking into an interim CEO, a new CEO, and two different bosses in her first six months taught her more than any stable role could
• The Nando's lesson: how a global brand with deep purpose and a dream job on paper became the clearest signal that career decisions can't be made without factoring in where you are in your personal life
• Why Jennifer puts almost no weight on how long someone stayed at a company when she's hiring — and what she looks for instead (hint: it's not the polished pitch)
• How Jennifer thinks about the career ladder versus the career zigzag — and why she believes knowing your north star matters more than following a prescribed path upward
• What it actually takes to revive a nostalgic legacy brand like Clearly Canadian for a generation that never grew up with it — and why that challenge is the one she's most excited to unlock
• The interview process at Nando's that included a five-hour psychology assessment in London with jet lag — and what Jennifer says she learned about herself from it

Episode Highlights:

00:00 - Reviving a Legacy Brand

00:25 - Podcast Premise and Intro

00:50 - Meet Jennifer Blackburn – Clearly Canadian CMO

01:42 - Nostalgia Stories and Brand Magic

04:56 - From Doctor Dreams to Marketing

06:19 - Unilever Training Ground

08:36 - Marketing Then vs Now

10:26 - Pivot to Tech at Skip

12:23 - Risk Support and Overwhelm

13:35 - Choosing Growth Together

16:02 - From Skip to Clearly Canadian

16:51 - Wrong Turns in Life

21:52 - Hiring Mindset on Short Tenures

23:26 - Interviewing for Authenticity

25:41 - Most Intense Interview Experience

27:00 - Working Parenthood and Energy

27:57 - Work Life Balance Lessons

29:18 - Career Pivots And North Star

30:47 - Transition Season At Home

32:31 - Favorite Clearly Canadian Flavor

33:09 - Gut Check On C Suite Paths

35:16 - Switching Industries And Growth

39:10 - Travel For Work Reality Check

42:25 - Remote Work And Productivity Debate

44:04 - Sleep Time Zones And Car Rules

46:58 - What We Missed And Wrap Up

48:09 - Podcast Wrap Up

Resources Mentioned:

• Clearly Canadian — the brand Jennifer currently leads as CMO; https://clearlycanadian.com/
• SkipTheDishes — Canadian food delivery tech company
• Canadian Tire — Canadian retail company
• Nando’s — global restaurant brand
• Unilever — global consumer goods company
• PepsiCo — multinational food and beverage corporation, referenced as a training ground for CPG marketers alongside Unilever
• Kroger — US grocery retailer

Quotes:

“And I think there’s tends to be scrutiny on that versus why stay longer if it's not working for you?” - Jennifer Blackburn

“ Doing virtual homework with my daughter at three in the morning buy time. And she's like, mommy, why is it dark where you are? And it's bright where I am.” - Jennifer Blackburn

“ I think sometimes you think the trajectory must go straight up at all times or else I'm not achieving.” - Sarah Jeanneault

“ It is really kind of looking internally first to say like, what do you want, like what's your north star in what your career, and this might be a stepping stone to your end. It may not be, you know, the, the, the whole way there.” - Jennifer Blackburn

“ It's not just about the job, it's not just about the company. It's also about how does this fit into your, your lifestyle and what tradeoffs are you able or willing to make or not.” - Jennifer Blackburn

“ People being honest and genuine versus trying to be pitchy and selling of their experience. I really try and look for that humbleness, that authenticity.” - Jennifer Blackburn

Jennifer Blackburn is the CMO of Clearly Canadian, where she leads the work of evolving a beloved legacy brand for the next generation of consumers. Her career spans CPG, retail, foodservice, and tech — including brand leadership roles at Unilever, PepsiCo, Nandos, Canadian Tire, and SkipTheDishes. Known for building high-performance teams and revitalizing iconic brands, she brings an entrepreneurial mindset to every organization she joins, whether it's a multinational or a private equity-backed startup.

Connect with Jennifer Blackburn: https://www.linkedin.com/in/jennifer-blackburn-9b5958a/

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This show is produced by Twisted Spur Media Ltd.

Disclaimer: The views, information, or opinions expressed by guests during Why To The Way Podcast are solely those of the individuals involved and do not necessarily represent those of Sarah Jeanneault, Twisted Spur Media Ltd. and/or her affiliates. Sarah Jeanneault, Why To The Way Podcast, and Twisted Spur Media Ltd. are not responsible for and do not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.